A Rare Development Opportunity on Maryland’s Eastern Shore

Opportunities like this are becoming increasingly rare in today’s market.

Located just minutes from Downtown Chestertown, 0 Round Top Road offers 5.81 acres of cleared, level land positioned along a key commercial corridor. With Suburban Commercial (SC) zoning, this property presents a unique chance for investors, developers, and business owners to secure land in one of the Eastern Shore’s most desirable and steadily growing areas.

Strategic Location with Real Potential

Location is everything in real estate. This property delivers.

Round Top Road sits in a highly accessible area just outside the historic core of Chestertown. It offers excellent visibility and convenience while…

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A Property That Offers More Than Just Land — It Offers Possibility

Opportunities like this are becoming increasingly rare on Maryland’s Eastern Shore.

Located at 1517 Dudley Corners Road in Millington, this unique offering combines 12 acres of land, two homes, and multiple outbuildings into one compelling package—perfect for buyers looking to create a homestead, invest, or simply expand their lifestyle beyond the ordinary.

With approximately 2,948 square feet, 6 bedrooms, and 3 full bathrooms, the main residence provides the space needed for multi-generational living, rental potential, or flexible use.

But what truly sets this property apart is not just what’s here—it’s what it can become.

A True Eastern Shore Homestead Opportunity

This…

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If you’ve been searching for a true boater’s paradise on Maryland’s Eastern Shore, 110 Channel Marker Way #203 in Grasonville delivers the perfect blend of luxury, convenience, and waterfront lifestyle.

Located just over the Bay Bridge, this three-level waterfront residence offers sweeping Chesapeake views from every floor — all easily accessed by your private elevator. Every detail reflects thoughtful design and impeccable maintenance.

Waterfront Living Designed Around the View

From the moment you enter, the first floor feels warm and inviting. A fireplace anchors the living space, flowing seamlessly into the open kitchen — ideal for entertaining after a day on the water. A guest bedroom with an ensuite full bath (currently used as an…

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2025 was a year highlighted by growth and successful execution for my business here on the Eastern Shore of Maryland. Each year Coldwell Banker announces its highest producing agents worldwide and I am proud to announce that much like in 2024, not only am I our office's top producer but I am also recognized as one of the top 4% of agents internationally. Every sale for me represents either a new relationship or growing relationship here on the Eastern Shore. Whether you are interesting in improving your quality of life by buying here or would like to maximize your return by selling with my representation, I am here for you via phone at 443-480-4275 or email at murphy@cbchesapeake.com.

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Historic Farm Sold

This another example of successful preparation, marketing, and sale through my results driven and relationship based approach to real estate sales. Historic "Mount Mills" was patented in 1665 and the Sally Harris Mill House was constructed in 1793. This property is over 31 acres with pasture, creeks, and forest. This historically significant property sits high up on the banks of Madam Alice Branch, a tributary of the Wye River. The 18th Century charm is represented with the cedar shake gambrel roof, flemish bond brickwork, and 5 fireplaces. This property represents the fine aspects of Eastern Shore life. Wildlife here is abundant with birds, perch, deer, and turkeys all evidenced on the property. The heated pool, gardens, and privacy makes this the…

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Effortless One-Floor Living in Chestertown – 204 Rolling Rd Comfort, Convenience, and Chestertown Charm

Located just minutes from downtown Chestertown, 204 Rolling Rd is a beautiful example of how modern comfort can blend seamlessly with Eastern Shore lifestyle. This three-bedroom, two-bath ranch-style home offers nearly 2,300 sq ft of thoughtfully designed living space — all on one level — making it perfect for anyone seeking low-maintenance living without sacrificing style or space. Spacious Living, Inside and Out From the moment you walk in, you’ll notice how bright and welcoming this home feels. The open flow between the living, dining, and kitchen areas creates a warm, connected atmosphere that’s perfect for entertaining or relaxing with family.

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First Floor

A Landmark Home in the Heart of Chestertown’s Historic District

Few homes capture the spirit of Chestertown quite like this. Built in 1863, the residence at 105 High Street stands as a rare opportunity to own a piece of Eastern Shore history — thoughtfully restored for modern living. This five-bedroom, four-and-a-half-bath Victorian combines 19th-century craftsmanship with 21st-century comfort. From the moment you step inside, you’re greeted by soaring ceilings, intricate millwork, and a grand three-story staircase that defines the home’s timeless character.

A Blend of History and Modern Comfort

Every detail tells a story. The chef’s kitchen has been fully updated with stainless appliances and elegant finishes, offering the perfect…

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101 S. Mill Street is on a quiet block just around the corner from the shops, galleries, and restaurants of Chestertown's Historic District and just 3 blocks from the waterfront promenade. The spacious rear yard with hobby shed is a gardener's delight. Historic charm with a modern floor plan is the theme here. This seller was able to quickly prepare, market, and sell his property for over asking price in the first week.  If you are thinking of buying in Chestertown please make sure to utilize the community pages on the website as a resource. If you live in Chestertown and are considering selling or just want to know how much your home could currently sell for, please visit my seller page for a private consultation.

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This amazing contemporary with sweeping views of Still Pond Creek in Worton just sold for over asking price and was only on the market for several days. This area of Kent County provides peace and tranquility with high banks alleviating flood concerns and houses that are perched high up providing incredible sightseeing. Wildlife are abundant here making it perfect for nature enthusiasts. Still Pond Creek itself provides great opportunity for boaters as well as it dumps directly into the Chesapeake Bay. This means that here you can leave your protected dock on the calm creek and be in vast open waters for fishing or sailing within minutes. The garage and updated dock were other great benefits of this property as life on the Eastern Shore comes…

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SOLD - Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Queen Anne’s County. Cozy, comfortable home welcomes you with wrap-around waterviews in a serene wooded setting. With convenient single level living, the three bedroom one-and-half bath home offers an open flowing floorplan bright with natural light and custom wood detail. Relax and enjoy views from the large screened porch or stroll down to your dock and floating dock for boating, fishing and water activities. Located in the popular waterfront community of Chester Harbor you are a walk away from the community dock and picnic area. This property is a little gem located just 3-miles from downtown historic Chestertown. Chestertown is located about 90 minutes…

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